Don’t get me wrong. I’m sure we could talk about at least 10 other things that need your attention when you are turning your side-gig into your main-gig, but as someone who made that leap (and sometimes feels as if she is still on a ledge looking down), I noticed 5 areas that really affected me.

I’m sharing them with you in hopes that they will help you of course, but I’m also really interested to know your take on some of these things and what areas really affected you.

Please don’t hesitate to talk about it in the comments.

Iron can’t sharpen iron if it’s a the only pole out there. (That was pretty bad, but it sounded really good in my head!)

Check out 5 key areas to think about when turning your side-gig into your main-gig. #freelance #entrepreneur Click To Tweet

1. Accounting & Taxes


If I’m an avenger, then Accounting & Taxes are the aliens/evil geniuses that I’m fighting against.

At least that is how I feel.

I taught high school for six years. (Oh, the joys of getting cursed out and hated!)

After that, I was a program director for a non-profit where I managed about 150 volunteers.

Both professions provided me with stability while I did graphic design on the side.

After venturing out from under the safety net of a full-time job, I realized that if I planned on being an actual adult, I would need to be able to prove my income in a way that a financial institution would accpt. Here’s what I did (not all at once, I made a number of mistakes along the way):

1) Established a business bank account along with my PayPal. At first I thought my PayPal was good enough until I tried to buy a car and despite my pretty PayPal reports that I printed off (in color) and my official statements from their website, the creditor wouldn’t accept them as proof.

Instead, I had to open a business checking account and start paying myself regularly from my PayPal, so I could have actual bank statements. The payments were small at first, but they got bigger (Come on somebody!)

2) Selected an easy online accounting software that would allow me to keep track of everything. I personally found that Wave did the job for me. It works well for freelancers. I have been told that Freshbooks works really well for small business owners.

*For an unbiased, thorough review of Wave, check this out from the content team over at Cloudwards.

3) Researched my profession and what it meant to my state. After checking the comptroller’s website, I found out that graphic design and web design services (for the most part) require that I pay sales taxes if my clients are in Texas as well.

So, I started calculating those quarterly and paying them. And just so you know, when you forget to pay them, a nice, little man may come knocking at your door and ask you to pay them. Oh yes! I know this first hand. Apparently the Comptroller’s office feels that a phone call isn’t personal enough.

4) Started saving and recording everything. Now when I make a purchase for my business, I save the receipt. When I go to meet someone, I track my mileage. These are all things I didn’t care about when this was just my side hustle, but now it isn’t.

2. Branding

The way I used to present my brand to the world was too impersonal and corporate looking.

It still had my colors (which I love) and it was definitely functional and attractive, but there was no way that I could live up the type of brand it portrayed.

That website represented an entire design team when I needed something that represented exactly what you were getting . . . me.

Your branding sets the expectation to your audience of who they are dealing with, and you want that to be positive and real in every way.

For example, if my client knows that I’m a mother of 5 and can only schedule a call after 6pm, then it is not annoying that they may hear Mickey Mouse Clubhouse in the background.


3. Time Management

Boy is this a big one!

I mentioned my 10-minute moments of productivity in Freelancing While in Freefall and that is still a go-to for me.

Time management is one of those beasts that never goes away, like high fructose corn syrup or love handles (those are probably related).

And I strongly believe that the way you go about time management depends on your personality, work habits, and current life status. Honestly, if I go to Amazon and search time management, the amount of information is crazy. Here are a few strategies that helped me:

1) Determining my constants and my variables. This really helps me sort things out and get things done. To make it quick, I know that my constants aren’t going anywhere, so I prioritize them and do what I have to do, letting me know just how much time I have to devote to other things (my variables).

2) Organized my world for easy navigation. I cleaned up my computer, made sure that everything in my house had a place to go (or it got tossed), and worked with some really awesome resources like Evernote, Azendoo, and Asana to collaborate with others and keep my tasks in line. Now my main business organization tool is 17Hats. I love it. I even wrote a post with it in mind. Check out how you can stay organized with this video review of

3) Outsourced my weaknesses. Be careful. Don’t pigeon hole your thinking here. I’m talking about outsourcing ANYTHING that opens up time for you. That could mean getting help with your house work once a week, child care, design work, emails, etc…

4) Stayed honest with myself. I could tell you that this stuff ALWAYS works, but it doesn’t. Not for me anyway. One of the best ways I manage my time is by recognizing when I’m stressed out or just not loving life and I CHOOSE to be productive anyway.

4. Communication

Who did you tell about your transition and what do those people really think that means?

When I told my husband I was developing a course to help people design their own brand identities, he said, “That’s great babe.”

About a week later, he asked, “You finished your course yet?” I’m sure the look I gave him while sitting in my pile of laundry with a baby on my lap and another one calling me name wasn’t a nice one, but I had to remember that he had no clue what went into my world and my work.

Open communication with the people you are working with or with the people you are closest to on a personal level is key when transitioning to this new life.

You have to set realistic expectations of your availability and your needs, and be careful not to undermine those relationships.

No amount of money can replace the people closest to you and what they bring to your life. Just ask a rich, lonely, miserable person.

5. Social Media

Honestly, I’m one of those people who would miss out on all of the Internet amazement if it weren’t for my business. I don’t naturally gravitate towards social media, which means it takes real work for me to keep up.

However, once I ventured out there on my own, I found out how important social media really was.

First, people check your accounts to see how many other people interact with your company and factor that in when deciding whether or not to deal with you.

Second, you generate leads and followers through your interactions on social media.

And third, you find your peeps when you are engaged in social media and by peeps, I mean people you can support you, teach you, collaborate with you and ultimately know more than anyone what you deal with while growing your business. They know because they are doing it too and appreciate your support in return.

Of course, these relationships do not even come close to replacing the ones you have offline, but you never know who you will meet and how it will impact your life.

There were some very specific things that helped me when starting out on social media for business. I’m not saying that I’m balling when it comes to followers but in just 6 months (with no paid help), I increased my Twitter and Instagram followers 6 times over.

Here is what I did:

  • I used a service like Feedly to read my favorite blogs and schedule them for sharing through a service like Hootsuite
  • I scheduled about 6-10 tweets a day including my own stuff and one to two posts for Facebook
  • I took more time to design or plan my posts for Instagram and Pinterest and tried to post at least 4-5 times a week.
  • I retweeted/shared other people’s stuff as much as possible
  • I made sure my accounts matched my branding for my business

Gaining your Independence

Part of that is taking care of things yourself. If you want more resources, check out my online courses that teach you how to design for your business


design templates and resources that allow you to create awesome information products.

Now it’s your turn!

What were your toughest areas and how did you overcome them to start working independently? OR What are you most afraid of when you think of taking that plunge into the independent deep?

Share the Knowledge!


  • Emily says:

    I’ve been working my tail off the past year and a half trying to move 100% away from the 9-5. Right now I’m only working a “day job” part time, but my hope is to be 100% independent by the end of this year. Thanks for all the great tips!

    • Brittany says:

      I feel ya Emily! You keep working your tail off. As long as you keep recalibrating your priorities to ensure you have them all in the right order, you can gain that independence in the right way. Keep me updated. I love to hear how people handle their own craziness!

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